GB1101931A - Improvements in or relating to new indolyl pyrrolidinone compounds and the manufacture thereof - Google Patents
Improvements in or relating to new indolyl pyrrolidinone compounds and the manufacture thereofInfo
- Publication number
- GB1101931A GB1101931A GB15489/65A GB1548965A GB1101931A GB 1101931 A GB1101931 A GB 1101931A GB 15489/65 A GB15489/65 A GB 15489/65A GB 1548965 A GB1548965 A GB 1548965A GB 1101931 A GB1101931 A GB 1101931A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- benzyl
- compounds
- indolyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Novel 5-(indolyl)-2-pyrrolidinones of the formula <FORM:1101931/C2/1> where R is C1- 4 alkyl or benzyl, R1 is hydrogen, C1- 4 alkyl or benzyl, and R2 and R3 are hydrogen, C1- 4 alkyl, C1- 4 alkoxy, or halogen, are prepared by reacting an appropriate indolyl Grignard reagent with an appropriate N-substituted succinimide, subjecting the resulting N-substituted - g - oxoindole - 3 - butyramide of the formula <FORM:1101931/C2/2> to catalytic hydrogenation or reduction with an alkali metal borohydride, and dehydrating and cyclizing the resulting N-substituted-g -hydroxy - indole - 3 - butyramide by heating under azeotropic conditions in the presence of an acid catalyst to form a compound of the first general formula above, wherein R1 is hydrogen. The compounds wherein R1 is alkyl or benzyl are prepared by reacting the compounds wherein R1 is hydrogen with an alkyl or benzyl halide in the presence of an alkaline condensing agent and an inert liquid medium. The compounds have anti-viral activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US366647A US3291807A (en) | 1964-05-11 | 1964-05-11 | Process for production of 5-(indol-3-yl)-2-pyrrolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1101931A true GB1101931A (en) | 1968-02-07 |
Family
ID=23443915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15489/65A Expired GB1101931A (en) | 1964-05-11 | 1965-04-12 | Improvements in or relating to new indolyl pyrrolidinone compounds and the manufacture thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3291807A (en) |
| CH (1) | CH471140A (en) |
| DE (1) | DE1620595A1 (en) |
| GB (1) | GB1101931A (en) |
| IL (1) | IL23389A (en) |
| NL (1) | NL6505983A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1589965A (en) * | 1976-09-22 | 1981-05-20 | Ici Ltd | Fungicidal compositions and processes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2946805A (en) * | 1957-05-20 | 1960-07-26 | Gen Aniline & Film Corp | Synthesis of 2-pyrrolidone |
| SU119189A1 (en) * | 1958-10-01 | 1958-11-30 | Н.А. Дзбановский | The method of obtaining (indolyl-3) -gamma-butyric acid |
-
1964
- 1964-05-11 US US366647A patent/US3291807A/en not_active Expired - Lifetime
-
1965
- 1965-04-12 GB GB15489/65A patent/GB1101931A/en not_active Expired
- 1965-04-19 IL IL23389A patent/IL23389A/en unknown
- 1965-05-05 CH CH632765A patent/CH471140A/en not_active IP Right Cessation
- 1965-05-06 DE DE19651620595 patent/DE1620595A1/en active Pending
- 1965-05-11 NL NL6505983A patent/NL6505983A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL23389A (en) | 1969-01-29 |
| DE1620595A1 (en) | 1970-02-12 |
| US3291807A (en) | 1966-12-13 |
| CH471140A (en) | 1969-04-15 |
| NL6505983A (en) | 1965-11-12 |
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